title: Synthesis and antimycobacterial activity of novel thiadiazolylhydrazones of 1-substituted indole-3-carboxaldehydes.
abstract: A series of novel thiocarbohydrazones of substituted indoles and their corresponding thiadiazole derivatives were prepared, and their structures were confirmed by different analytical and spectroscopic methods. The derivatives were prepared by a sequential synthetic strategy including substitution at N-1 position of indole ring by various aliphatic and benzylic substituents, followed by condensation with thiocarbohydrazide, and finally cyclization by triethyl orthoformate. The derivatives were tested for their antimycobacterial activity against Mycobacterium bovis BCG, and the results revealed that among the synthesized compounds, thiadiazole derivatives 4e, 4f, 4n, 4p, 4q, and 4t exhibited the highest activity with IC₅₀ value of 3.91 μg/mL. The results indicate that the thiadiazole moiety plays a vital role in exerting antimycobacterial activity.
authors.affiliation: Department of Medicinal Chemistry, School of Pharmacy, Zanjan University of Medical Sciences, Gavazang Road, Zanjan 45139-56184, Iran.
authors.forename: Kamaleddin Haj Mohammad Ebrahim
authors.initials: KH
authors.lastname: Tehrani
authors.forename: Vida
authors.initials: V
authors.lastname: Mashayekhi
authors.forename: Parisa
authors.initials: P
authors.lastname: Azerang
authors.forename: Soroush
authors.initials: S
authors.lastname: Sardari
authors.forename: Farzad
authors.initials: F
authors.lastname: Kobarfard
authors.forename: Kobra
authors.initials: K
authors.lastname: Rostamizadeh
mesh_terms: D000818:Animals; D000995:Antitubercular Agents / Q000138:chemical synthesis / Q000494:pharmacology; D045744:Cell Line, Tumor; D002470:Cell Survival; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D051379:Mice; D008826:Microbial Sensitivity Tests; D009163:Mycobacterium bovis / Q000187:drug effects*; D013329:Structure-Activity Relationship; D013830:Thiadiazoles / Q000737:chemistry*
chemical_list: D000995:Antitubercular Agents; D007211:Indoles; D013830:Thiadiazoles; C012381:indole-3-carbaldehyde; C030374:indole
keywords: antimycobacterial; indole; structure-activity relationship; thiadiazolylhydrazone; thiosemicarbazones